US2015011508A1PendingUtilityA1
Compounds and compositions as c-kit kinase inhibitors
Est. expirySep 1, 2031(~5.1 yrs left)· nominal 20-yr term from priority
Inventors:Xiaodong LiuXiaolin LiJon LorenValentina MolteniJuliet NabakkaBao NguyenHank Michael James PetrassiVince Yeh
A61P 37/06A61P 9/12A61P 9/00A61P 3/10A61P 37/08A61P 43/00A61P 29/00A61P 3/00C07D 471/04A61P 11/00A61K 31/4245A61P 11/02A61P 17/00A61P 1/16A61P 17/04A61P 1/00C07F 9/6561A61P 11/06
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Claims
Abstract
The invention provides compounds of formulae (I) and (II) and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.
Claims
exact text as granted — not AI-modified1 . A compound of Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof:
wherein:
m is 1 and R 20 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, deuterium, deuterated C 1 -C 6 alkyl, —CN, —(CR 9 2 ) n OR 4 , —C(O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , R 8 , —(CR 9 2 ) n R 8 , —((CR 9 2 ) n O) t R 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n C(═O)R 4 , —C(═O)N(R 4 ) 2 , —N(R 4 ) 2 , —C(═S)N(R 4 ) 2 , —(CR 9 2 ) n OR 4 , —OW and —(CR 9 2 ) n CN,
or m is 4 and R 20 is deuterium;
R 1 is selected from C 1 -C 6 alkyl and halo;
each R 11 is independently selected from H, halo and C 1 -C 6 alkyl;
L 1 is a bond, —NH— or —C(O)NH—;
R 2 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkenyl, —(CR 9 2 ) n OR 4 , —(CR 9 2 ) n R 6 , —(CR 9 2 ) n S(═O) 2 NR 4 2 , —(CR 9 2 ) n CN, —(CR 9 2 ) n C(═O)R 4 , —(CR 9 2 ) n OC(═O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , —(CR 9 2 ) n C(═O)NR 4 2 , —(CR 9 2 ) n OC(═)ONR 4 (CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n O(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n OCR 9 R 6 R 6 , —(CR 9 2 ) n CR 9 R 5 R 6 , —(CR 9 2 ) n CR 5 R 6 R 6 , —(CR 9 2 ) n CR 9 R 6 OC(O)(CR 9 2 ) n NR 4 2 , —(CR 9 2 ) n OC(O)(CR 9 2 ) n NR 4 2 , —CR 9 R 5 R 6 , —CR 9 R 9 R 5 , —CR 9 R 6 NR 4 2 , —(CR 9 2 ) n NR 4 2 , —NR 4 (CR 9 2 ) n OR 4 , —NR 4 (CR 9 2 ) n R 6 , —NR 4 (CR 9 2 ) n R 4 , —(CR 9 2 )NR 4 C(═O)R 4 , —(CR 9 2 ) n NR 4 C(═O)OR 4 , —(CR 9 2 )NR 4 C(═O)NR 4 2 , —(CR 9 2 )NR 4 C(═O)R 6 , —(CR 9 2 ) n NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n OR 4 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n OR 4 , —CR 5 R 5 NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 5 C(═O)R 6 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n R 6 , —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 11 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n O(CR 9 2 ) n R 6 , and —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 6 ;
each R 4 is independently selected from H and C 1 -C 6 alkyl;
each R 5 is independently selected from —NHC(O)OR 4 , —OP(O)(OR 4 ) 2 and —(CR 9 2 ) n OR 4 ;
each R 6 is a C 1 -C 6 haloalkyl;
each R 9 is independently selected from H and C 1 -C 6 alkyl;
R 8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, a substituted C 3 -C 8 cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 8 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, halo, —(C(R 9 ) 2 ) n OR 4 , —C(O)NR 4 2 —NR 4 2 , —R 10 , —(C(R 9 ) 2 ) n R 19 , —(C(R 9 ) 2 ) n C(O)OR 4 , —C(O)OR 4 , —(C(R 9 ) 2 ) n C(O)NR 4 2 , —C(O)NR 4 (C(R 9 ) 2 ) n R 19 , —(C(R 9 ) 2 ) n C(O)NR 4 (C(R 9 ) 2 ) n R 19 , —(C(R 9 ) 2 ) n C(O)NR 4 (C(R 9 ) 2 ) n OR 4 , —C(O)NR 4 (C(R 9 ) 2 ) n OR 4 , —C(O)OR 4 , —C(O)R 4 and —S(O) 2 R 4 ;
R 10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, and a substituted C 3 -C 8 cycloalkyl,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 10 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, and —(C(R 9 ) 2 ) n OR 4 ;
t is 1, 2 or 3, and
each n is independently selected from 1, 2, 3 and 4.
2 . The compound of claim 1 wherein:
m is 1 and R 20 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, deuterium, deuterated C 1 -C 6 alkyl, —CN, —(CR 9 2 ) n OR 4 , —C(O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , R 8 , —(CR 9 2 ) n R 8 , —((CR 9 2 ) n O) t R 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n C(═O)R 4 , —C(═O)N(R 4 ) 2 , —(CR 9 2 ) n OR 4 , —OR 4 and —(CR 9 2 ) n CN,
or m is 4 and R 20 is deuterium;
R 1 is selected from C 1 -C 6 alkyl and halo;
each R 11 is independently selected from H, halo and C 1 -C 6 alkyl;
L 1 is a bond, —NH— or —C(O)NH—;
R 2 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkenyl, —(CR 9 2 ) n OR 4 , —(CR 9 2 ) n R 6 , —(CR 9 2 ) n S(═O) 2 NR 4 2 , —(CR 9 2 ) n CN, —(CR 9 2 ) n C(═O)R 4 , —(CR 9 2 ) n OC(═O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , —(CR 9 2 ) n C(═O)NR 4 2 , —(CR 9 2 ) n OC(═O)NR 4 (CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n O(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n OCR 9 R 6 R 6 , —(CR 9 2 ) n CR 9 R 5 R 6 , —(CR 9 2 ) n CR 5 R 6 R 6 , —CR 9 R 5 R 6 , —CR 9 R 9 R 5 , —CR 9 R 6 NR 4 2 , —(CR 9 2 ) n NR 4 2 , —NR 4 (CR 9 2 ) n OR 4 , —NR 4 (CR 9 2 ) n R 6 , —NR 4 (CR 9 2 ) n R 4 , —(CR 9 2 )NR 4 C(═O)R 4 , —(CR 9 2 ) n NR 4 C(═O)OR 4 , —(CR 9 2 )NR 4 C(═O)NR 4 2 , —(CR 9 2 )NR 4 C(═O)R 6 , —(CR 9 2 ) n NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n OR 4 , —CR 5 R 5 NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 5 C(═O)R 6 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n R 6 , —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 11 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n O(CR 9 2 ) n R 6 , and —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 6 ;
each R 4 is independently selected from H and C 1 -C 6 alkyl;
each R 5 is independently selected from —NHC(O)OR 4 , —OR 4 and —(CR 9 2 ) n OR 4 ;
each R 6 is a C 1 -C 6 haloalkyl;
each R 9 is independently selected from H and C 1 -C 6 alkyl;
R 8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, a substituted C 3 -C 8 cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 8 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, halo, —(C(R 9 ) 2 ) n OR 4 , —C(O)NR 4 2 —NR 4 2 , —R 10 , —(C(R 9 ) 2 ) n R 10 , —OR 4 , —(C(R 9 ) 2 ) n C(O)OR 4 and —S(O) 2 R 4 ;
R 10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, and a substituted C 3 -C 8 cycloalkyl,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 10 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, and —(C(R 9 ) 2 ) n OR 4 ;
t is 1, 2 or 3, and
each n is independently selected from 1, 2, 3 and 4.
3 . The compound of claim 1 , wherein the compound is a compound of Formula (Ia), Formula (IIa), Formula (Ib) or Formula (IIb):
wherein:
m is 1 and R 20 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, deuterium, deuterated C 1 -C 6 alkyl, —CN, —(CR 9 2 ) n OR 4 , —C(O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , R 8 , —(CR 9 2 ) n R 8 , —((CR 9 2 ) n O) t R 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n C(═O)R 4 , —C(═O)N(R 4 ) 2 , —(CR 9 2 ) n OR 4 , —OR 4 and —(CR 9 2 ) n CN;
or m is 4 and R 20 is deuterium;
R 1 is selected from C 1 -C 6 alkyl and halo;
each R 11 is independently selected from H, halo and C 1 -C 6 alkyl;
R 2 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 8 alkenyl, —(CR 9 2 ) n OR 4 , —(CR 9 2 ) n R 6 , —(CR 9 2 ) n S(═O) 2 NR 4 2 , —(CR 9 2 ) n CN, —(CR 9 2 ) n C(═O)R 4 , —(CR 9 2 ) n OC(═O)R 4 , —(CR 9 2 ) n C(═O)OR 4 , —(CR 9 2 ) n C(═O)NR 4 2 , —(CR 9 2 ) n OC(═)ONR 4 (CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n O(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n OCR 9 R 6 R 6 , —(CR 9 2 ) n CR 9 R 5 R 6 , —(CR 9 2 ) n CR 5 R 6 R 6 , —CR 9 R 5 R 6 , —CR 9 R 9 R 5 , —CR 9 R 6 NR 4 2 , —(CR 9 2 ) n NR 4 2 , —NR 4 (CR 9 2 ) n OR 4 , —NR 4 (CR 9 2 ) n R 6 , —NR 4 (CR 9 2 ) n R 4 , —(CR 9 2 )NR 4 C(═O)R 4 , —(CR 9 2 ) n NR 4 C(═O)OR 4 , —(CR 9 2 )NR 4 C(═O)NR 4 2 , —(CR 9 2 )NR 4 C(═O)R 6 , —(CR 9 2 ) n NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n OR 4 , —CR 5 R 5 NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 5 C(═O)R 6 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n R 6 , —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 11 , —(CR 9 2 ) n NR 4 C(═O)(CR 9 2 ) n O(CR 9 2 ) n R 6 , and —(CR 9 2 ) n NR 4 C(═O)O(CR 9 2 ) n R 6 ;
each R 4 is independently selected from H and C 1 -C 6 alkyl;
each R 5 is independently selected from —NHC(O)OR 4 , —OR 4 and —(CR 9 2 ) n OR 4 ;
each R 6 is a C 1 -C 6 haloalkyl;
each R 9 is independently selected from H and C 1 -C 6 alkyl;
R 8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, a substituted C 3 -C 8 cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 8 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, halo, —(C(R 9 ) 2 ) n OR 4 , —C(O)NR 4 2 —NR 4 2 , —R 10 , —(C(R 9 ) 2 ) n R 10 , —(C(R 9 ) 2 ) n C(O)OR 4 and —S(O) 2 R 4 ;
R 10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C 3 -C 8 cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, and a substituted C 3 -C 8 cycloalkyl,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C 3 -C 8 cycloalkyl and substituted 4-6 membered heterocycloalkyl of R 10 are substituted with 1-3 substituents independently selected from C 1 -C 6 alkyl, and —(C(R 9 ) 2 ) n OR 4 ;
t is 1, 2 or 3, and
each n is independently selected from 1, 2, 3 and 4.
4 . The compound of claim 1 wherein R 1 is selected from —CH 3 and F.
5 . The compound of claim 1 , wherein R 1 is —CH 3 .
6 . The compound of claim 1 , wherein each R 11 is independently selected from H, F and —CH 3 .
7 . The compound of claim 1 , wherein each R 11 is H.
8 . The compound of claim 1 , wherein:
R 2 is selected from —(CR 9 2 ) n CN, —(CR 9 2 ) n NR 4 C(═O)OR 4 , —(CR 9 2 ) n OR 4 , —(CR 9 2 ) n C(═O)NR 4 2 , —(CR 9 2 ) n C(═O)R 4 , C 1 -C 6 alkyl, C 2 -C 8 alkenyl, —(CR 9 2 ) n CR 5 R 6 R 6 , —CR 5 R 5 NR 4 S(═O) 2 R 4 , —(CR 9 2 ) n NR 4 S(═O) 2 R 4 , —(CR 9 2 )NR 4 C(═O)R 6 , —(CR 9 2 ) n O(CR 9 2 ) n OR 4 , —(CR 9 2 ) n C(═O)OR 4 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n CR 9 R 5 R 6 , —NR 4 (CR 9 2 ) n R 6 , —NR 4 (CR 9 2 ) n R 4 , —(CR 9 2 ) n R 6 and —(CR 9 2 ) n OCR 9 R 6 R 6 .
9 . The compound of claim 1 , wherein:
R 2 is selected from —(CR 9 2 ) n CR 9 R 5 R 6 and —(CR 9 2 ) n OR 4 .
10 . The compound of claim 1 , wherein each R 4 is independently selected from H, methyl, ethyl, propyl, butyl, i-propyl and t-butyl.
11 . The compound of claim 1 , wherein each R 5 is independently selected from, —OR 4 and —(CR 9 2 ) n OR 4 .
12 . The compound of claim 1 , wherein each R 5 is independently selected from OH and —CH 2 OH.
13 . The compound of claim 1 , wherein each R 6 is independently selected from —CH 2 F, —CHF 2 , —CH 2 CHF 2 , —CH 2 CF 3 and —CF 3 .
14 . The compound of claim 1 , wherein each R 9 is independently selected from H, methyl and ethyl.
15 . (canceled)
16 . The compound of claim 1 , wherein R 2 is —C(CH 3 ) 2 CH 2 OH or —CH 2 CH 2 C(CH 3 )OHCF 3 .
17 . The compound of claim 1 wherein m is 1 and R 20 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, deuterated C 1 -C 6 alkyl, —CN, —(CR 9 2 ) n OR 4 , —R 8 , —(CR 9 2 ) n R 8 , —(CR 9 2 ) n O(CR 9 2 ) n R 6 , —(CR 9 2 ) n C(═O)R 4 , —(CR 9 2 ) n OR 4 and —OR 4 .
18 . The compound of claim 1 , wherein m is 1 and R 20 is selected from H, —F, —CH 3 , —CF 3 , —CD 3 , —CN, —OCHF 2 , —CH 2 CH 2 C(CH 3 ) 2 OH, —CH 2 OCH 2 CF 3 , —CH 2 CH 2 C(═O)CH 3 , —CH 2 OCH 3 and —OCH 3 .
19 . The compound of claim 1 , wherein m is 1 and R 20 is H or —CH 3 .
20 . (canceled)
21 . (canceled)
22 . The compound of claim 1 , wherein:
R 8 is selected from phenyl, morpholinyl, cyclopropyl, pyridinyl, pyridine-3-yl, pyridine-4-yl, pyrazolyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrrolyl, triazolyl, 1H-1,2,3-triazol-4-yl, 4H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, thiazolyl, thiazol-4-yl, thiazol-5-yl, isoxazolyl and isoxazol-4-yl, each of which is unsubstituted or each of which is substituted with 1-3 substituents independently selected from F, —CH 3 , —C(CH 3 ) 2 CH 2 OH, —CH 2 OCH 3 , —C(O)NHCH 3 , —NH 2 and —OCH 3 .
23 . (canceled)
24 . The compound of claim 1 selected from:
N-{5-[5-(2-cyanoethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl N-{2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl}carbamate;
N-{5-[5-(3-methoxypropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[2-(diethylcarbamoyl)ethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(3-oxobutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
ethyl 2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]acetate;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(2-ethoxyethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(ethoxymethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl N-[(1S)-1-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl]carbamate;
N-(5-{5-[(1R)-1-methoxyethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(1,3-dihydroxy-2-methanesulfonamidopropan-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(1R)-1-methanesulfonamidoethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}-N-methylcarbamate;
N-{5-[5-(ethanesulfonamidomethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl N-ethyl-N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
N-(5-{5-[(N-ethylmethanesulfonamido)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl N-ethyl-N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
N-(2-methyl-5-{5-[(2,2,2-trifluoroacetamido)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(propane-2-sulfonamidomethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl 2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]acetate;
N-(2-methyl-5-{5-[2-(2,2,2-trifluoroethoxy)ethyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
ethyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
propan-2-yl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
N-(2-methyl-5-{5-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2-ethoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-{[2-(propan-2-yloxy)ethoxy]methyl}-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-[5-(5-{[2-(tert-butoxy)ethoxy]methyl}-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[(3,3,3-trifluoropropanamido)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-fluoro-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
6-fluoro-N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
ethyl N-{[3-(3-{6-fluoroimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
2,2-difluoroethyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate;
methyl N-({3-[4-methyl-3-(7-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}imidazo[1,2-a]pyridine-3-amido)phenyl]-1,2,4-oxadiazol-5-yl}methyl)carbamate;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
6-(1-methyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{[5-(1-hydroxy-2-methylpropan-2-yl)-1,2,4-oxadiazol-3-yl]amino}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1,3-thiazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
6-(2,4-dimethyl-1,3-thiazol-5-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}imidazo[1,2-a]pyridine-3-carboxamide;
5,6,7,8-tetradeutero-N-{2-methyl-5-[5-(3-methylbut-2-en-1-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
5,6,7,8-tetradeutero-N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
5,6,7,8-tetradeutero-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
propan-2-yl 3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]propanoate;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-6-methoxyimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl}-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-6-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(pentan-2-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(morpholin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(2-oxo-1,3-oxazolidin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(2-oxopyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
7-cyclopropyl-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
7-fluoro-N-(5-{5-[(2-hydroxy-2-methylpropyl)(methyl)amino]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2-fluoroethyl)amino]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(2-methylpropyl)amino]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-fluoro-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
6-fluoro-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
6-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
5,6,7,8-tetradeutero-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(3,3,3-trifluoropropyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(4,4,4-trifluorobutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(2-methylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(3-methylpyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
6-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-fluoro-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-fluoro-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-fluoro-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-fluoro-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-methoxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
6-(2,4-dimethyl-1,3-thiazol-5-yl)-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-(2-fluoropyridin-3-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)pyridine-2-carboxamide;
N-(5-{5-[(2,2-difluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-(5-{[(1,3-difluoropropan-2-yl)oxy]methyl}-1,2,4-oxadiazol-3-yl)-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-{[(1,1,1-trifluoropropan-2-yl)oxy]methyl}-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(4-methyl-1,3-thiazol-5-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1,3,5-trimethyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide;
6-(1-methyl-1H-pyrrol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(4-methoxypyridin-3-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(2-aminopyridin-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl 2-[3,5-dimethyl-4-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1H-pyrazol-1-yl]acetate;
6-[5-(1-hydroxyethyl)-4-methyl-1,3-thiazol-2-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(4,5-dimethyl-1,3-thiazol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(1-{[(2-hydroxyethyl)carbamoyl]methyl}-3,5-dimethyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-[3,5-dimethyl-1-({[2-(morpholin-4-yl)ethyl]carbamoyl}methyl)-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-carbamothioyl-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-hydroxyethyl)-4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-thiazole-5-carboxamide;
4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[3-(4-methylpiperazin-1-yl)propyl]-1,3-thiazole-5-carboxamide;
4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(morpholin-4-yl)ethyl]-1,3-thiazole-5-carboxamide;
8-amino-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxylic acid;
4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-thiazole-2-carboxamide;
2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl2-aminoacetate;
(2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl(2R)-2-amino-3-methylbutanoate;
(2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl (2R)-2-amino-3-methylbutanoate;
7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
6-[1-(2-hydroxyethyl)-3,5-dimethyl-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
6-(3-methyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N,4-dimethyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide;
6-{3,5-dimethyl-1-[(methylcarbamoyl)methyl]-1H-pyrazol-4-yl}-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
ethyl 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxylate;
4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(morpholin-4-yl)ethyl]-1,3-thiazole-2-carboxamide;
N-(2-hydroxyethyl)-4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxamide;
4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxamide;
6-[2-(hydroxymethyl)-4-methyl-1,3-thiazol-5-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[1-(2,2,2-trifluoroethoxy)ethyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
dimethyl (2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl phosphate;
{[(2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl]oxy}phosphonic acid;
dimethyl (2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl phosphate;
{[(2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl]oxy}phosphonic acid, and
1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl (2S)-2-aminopropanoate.
25 . The compound of claim 1 selected from:
N-(5-{[5-(1-hydroxy-2-methylpropan-2-yl)-1,2,4-oxadiazol-3-yl]amino}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide, and
7-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide.
26 . A pharmaceutical composition comprising a therapeutically effective amount a compound of claim 1 and a pharmaceutically acceptable carrier.
27 . (canceled)
28 . (canceled)
29 . (canceled)
30 . (canceled)
31 . (canceled)
32 . (canceled)
33 . (canceled)
34 . (canceled)
35 . (canceled)Join the waitlist — get patent alerts
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